A convenient approach to the design and synthesis of indolo[3,2-c]coumarins via the microwave-assisted Cadogan reaction

Tetrahedron Letters

Volumn 54, Issue 42, 2013, Pages 5734-5738

  Irgashev, Roman A ^a   Karmatsky, Arseny A ^a   Slepukhin, Pavel A ^a   Rusinov, Gennady L ^a,b   Charushin, Valery N ^a,b  

^a INSTITUTE OF ORGANIC SYNTHESIS   (Russian Federation)

^b URAL FEDERAL UNIVERSITY   (Russian Federation)

Author keywords

3 Aryl coumarins; Cadogan reaction; Indolo 3,2 c coumarins; Microwave assisted synthesis; Reductive cyclization; Salicylaldehydes

Indexed keywords

COUMARIN DERIVATIVE; SALICYLALDEHYDE;

ARTICLE; CRYSTAL STRUCTURE; CYCLIZATION; MELTING POINT; MICROWAVE IRRADIATION; SYNTHESIS; X RAY CRYSTALLOGRAPHY;

EID: 84883807778     PISSN: 00404039     EISSN: 18733581     Source Type: Journal    
DOI: 10.1016/j.tetlet.2013.08.030     Document Type: Article

References (33)

1. J.I.G. Cadogan Q. Rev. 6 1962 208 239
2. J.I.G. Cadogan, and M. Cameron-Wood Proc. Chem. Soc. 1962 361
3. P.J. Bunyan, and J.I.G. Cadogan Proc. Chem. Soc. 1962 78
4. P.J. Bunyan, and J.I.G. Cadogan J. Chem. Soc. 1963 42 49
5. J.I.G. Cadogan, and R.K. Mackie Chem. Soc. Rev. 3 1974 87 137
6. D.J. Varughese, M.S. Manhas, and A.K. Bose Tetrahedron Lett. 47 2006 6795 6797
7. E.C. Creencia, M. Kosaka, T. Muramatsu, M. Kobayashi, T. Iizuka, and T. Horaguchi J. Heterocycl. Chem. 46 2009 1309 1317
8. M. Roussaki, C.A. Kontogiorgis, D. Hadjipavlou-Litina, S. Hamilakis, and A. Detsi Bioorg. Med. Chem. Lett. 20 2010 3889 3892
9. S.U. Rehman, Z.H. Chohan, F. Gulnaz, and C.T. Supuran J. Enzyme Inhib. Med. Chem. 20 2005 333 340
10. Z.F. Mahmoud, T.M. Sarg, M.E. Amer, and S.M. Khafagy Die Pharm. 38 1983 486 487
11. A. Yacobi, and G. Levy J. Pharm. Sci. 64 1975 1995 1998
12. N.A. Pereira, B.M.R. Pereira, M.C. Nascimento, J.P. Parente, and W.B. Mors Planta Med. 60 1994 99 100
13. J.R. Hwu, R. Singha, S.C. Hong, Y.H. Chang, A.R. Das, I. Vliengen, E. De Clercq, and J. Neyts Antiviral Res. 77 2008 157 162
14. M.V.R. Reddy, M.R. Rao, D. Rhodes, M. Hansen, K. Rubins, F.D. Bushman, Y. Venkateswarlu, and D.J. Faulkner J. Med. Chem. 42 1999 1901 1907
15. J. Neyts, E. De Clercq, R. Singha, Y.H. Chang, A.R. Das, S.K. Chakraborty, S.C. Hong, S.-C. Tsay, M.-H. Hsu, and J.R. Hwu J. Med. Chem. 52 2009 1486 1490
16. K.S. Lee, H.J. Kim, G.H. Kim, I. Shin, and J.I. Hong Org. Lett. 10 2008 49 51
17. Y. Zhao, Q. Zheng, K. Dakin, K. Xu, M.L. Martinez, and W.-H. Li J. Am. Chem. Soc. 126 2004 4653 4663
18. C.C. Woodroofe, A.C. Won, and S. Lippard J. Inorg. Chem. 44 2005 3112 3120
19. K. Hara, Z.S. Wang, T. Sato, A. Furube, R. Katoh, H. Sugihara, Y. Dan-Oh, C. Kasada, A. Shinpo, and S. Suga J. Phys. Chem. B 109 2005 15476 15482
20. K. Hara, T. Sato, R. Katoh, A. Furube, Y. Ohga, A. Shinpo, S. Suga, K. Sayama, H. Sugihara, and H. Arakawa J. Phys. Chem. B 107 2003 597 606
21. K. Hara, Y. Tachibana, Y. Ohga, A. Shinpo, S. Suga, K. Sayama, H. Sugihara, and H. Arakawa Sol. Energy Mater. Sol. Cells 77 2003 89 103
22. G.G. Kuiper, J.G. Lemmen, B. Carlsson, J.C. Corton, S.H. Safe, P.T. van der Saag, B. van der Burg, and J.A. Gustafsson Endocrinology 139 1998 4252 4263
23. S. Sarveswaran, S.C. Gautam, and J. Ghosh Int. J. Oncol. 41 2012 2191 2199
24. S.M. Wong, S. Antus, A. Gottsegen, B. Fessler, G.S. Rao, J. Sonnenbichler, and H. Wagner Arzneimittelforschung 38 1988 661 665
25. N. Thasana, R. Worayuthakarn, P. Kradanrat, E. Hohn, L. Young, and S. Ruchirawat J. Org. Chem. 72 2007 9379 9382
26. T. Yao, D. Yue, and R.C. Larock J. Org. Chem. 70 2005 9985 9989
27. W. Stadlbauer, R. Laschober, and T. Kappe Monatsh. Chem. 122 1991 853 861
28. W. Stadlbauer, and T. Kappe Monatsh. Chem. 115 1984 467 476
29. G.N. Walker J. Am. Chem. Soc. 77 1955 3844 3850
30. www.ccdc.cam.ac.uk/data-request/cif.
31. Mercury 3.1, available from http://www.ccdc.cam.ac.uk/mercury/.
32. www.ccdc.cam.ac.uk/data-request/cif.
33. G.M. Sheldrick Acta Cryst. Sect. A 64 2008 112 122